Keeping Commerce Weird Podcast: What It Takes to Scale Without Breaking

Nobody thinks about integrations when everything is working.

Orders flow. Inventory updates. Products ship. The business keeps moving. Then something breaks.

In this episode of Keeping Commerce Weird, CEO of Commerce Travis Hess sits down with Jim Herbert, CEO of Patchworks, to discuss the systems, leadership decisions, and operational discipline that keep modern commerce running behind the scenes.

From scaling a SaaS company to navigating AI, APIs, and automation, Herbert shares a candid perspective on what it takes to build businesses that can grow without falling apart.

Here are the key insights from the discussion.

Keeping Commerce Weird Podcast Recap: CEO to CEO: How to Scale Without Snapping

Great leaders scale by letting go.

Travis Hess: What was the hardest mindset shift for you going from founder and operator to CEO?

Jim Herbert: “As you go through your career and move into leadership roles, you get better and better at delegation and making sure you've got experts around you who really know their piece.

Being a CEO is a constant game of whack-a-mole. There's always something out there. The biggest shift was figuring out how to rise above that and not get involved in everything.

I've got some knowledge of software sales. I've got some knowledge of technology. But at some point, you have to set boundaries and goals, let people run with it, and trust them to report back.

It's not being too involved. That's the real key thing.

And yes, it can be lonely. Who can you really talk to? Everyone has their own agenda. Whether it's your leadership team, your board, or your investors, there are conversations you can't always have openly. That's why having a network of other CEOs and operators matters so much.”

Key takeaway

Many leaders earn promotions because they're great at doing the work. The challenge comes when the job changes from execution to enablement. As businesses grow, success depends less on having all the answers and more on building teams that can operate without you. Leadership also comes with a less-discussed reality: the higher you climb, the smaller the circle of people who truly understand the decisions you're making.

Growth exposes what businesses are built on.

Hess: How does your leadership approach change as you go from supporting smaller businesses to brands like Gymshark and LVMH, where the stakes are much higher?

Herbert: “Part of dealing with customers of that size is having repeatable systems in place. You need to know how to deal with an NDA, a contract, and everything that comes with operating at that level.

Fundamentally, we're an integration platform. It should scale to any customer.

You have to change your leadership style because you've gone from being a transformation CEO to becoming more strategic. The more you've delegated into the teams and they're performing well, the more it allows you to put your head above the parapet and think about what's next.

From the product perspective, half of what we put in comes from customer and partner feedback. But what do we strategically need to do to stay ahead of the competition? What else do we need to do as a business? That's the step up we're in right now.”

Key takeaway

Scaling isn't just about adding customers. It's about building the systems, processes, and teams that can support growth without creating chaos. As organisations mature, leaders spend less time solving immediate problems and more time thinking about what's coming next.

AI is only as powerful as the systems behind it.

Hess: Where does AI genuinely help today, and where is it overblown?

Herbert: “We didn't want to go down the route of getting an AI domain name or just saying we are AI-first before anything really happened. The hype-based marketing is not how we roll.

We were at a point of saying, ‘Let's look at where the product's being used. Where can AI help?’

The first thing was scripting. Rather than writing a script, users were going off to ChatGPT, Gemini, or Claude. So we embedded that capability directly into the product.

APIs are the foundation of AI. The Model Context Protocol is kind of like an integration layer for AI. It allows us to integrate into tools like ChatGPT, Gemini, Claude, Slack, and others.

The API piece was really important. Putting AI capability on top of that is what allows operators within businesses to have real control of their business without having to pick up the phone or Slack a human.”

Key takeaway

The biggest AI opportunities aren't always customer-facing. In many cases, the real value comes from helping operators work faster, automate repetitive tasks, and make better use of the systems they already have. As AI adoption accelerates, businesses with connected data and modern infrastructure will be in a much stronger position to benefit from it.

Speed matters when businesses can control it.

Hess: Do agencies look at this the same way? Do they see platforms like yours as a way to create more value for customers, or do some view it as cannibalising billable hours?

Herbert: “The answer to that is both yes and no because some do and some don't.

There are agencies that really get it. They have strong pipelines, and we're answering a need for them, which is being able to win more projects and deliver more projects.

If you can do more with the team you've already got, you can win more, you can sell more, and that's a good thing. If you can do things more profitably and the customer gets it slightly cheaper, everybody's happy. It's a win-win situation.

There are agencies and systems integrators that bill by the hour, and we're seeing a little more resistance there. But in the last two years, more and more people are saying, ‘Yeah, I think we need to look at this.’

We've got leads to give them. Create a practise and start doing that.”

Key takeaway

Technology doesn't create value on its own. The real opportunity comes when businesses use it to remove friction, accelerate delivery, and free up teams to focus on higher-value work. As expectations continue to rise, the organisations that thrive will be the ones that embrace efficiency rather than protect old ways of working.

The final word

Ecommerce tends to celebrate the things customers can see: storefronts, campaigns, new technologies, and the experiences that drive conversion.

But as Jim Herbert reminds us, sustainable growth is usually determined by the things customers never see.

Whether it's leadership, integrations, operational processes, or AI, the common thread is reliability. Businesses can only move as fast as the systems supporting them, and growth has a way of exposing every weakness hiding beneath the surface.

As AI accelerates expectations and businesses look for new ways to scale, the winners won't simply be the ones adopting the latest technology. They'll be the ones building the foundations that allow that technology to deliver real value.

To hear the full conversation, watch “CEO to CEO: How to Scale Without Snapping” on YouTube or listen on Spotify.